Picking a Side
by Crittab
Summary: Inspired by a suitor of Abed's, Annie decides to send Jeff a risqué photo in hopes of persuading him to give her a shot. Rating bumped to M for chapter 2.
1. Chapter 1

**Title: **Picking a Side (1/1)

**Rating: **PG-13

**Spoilers/Warnings: **None

**Disclaimer: **I don't own Community, yo.

**Summary: **Inspired by a suitor of Abed's, Annie decides to send Jeff a risqué photo in hopes of persuading him to give her a shot.

**A/N: **Response to a Ficcy Sunday prompt from rashaka: Deciding that she can be daring for once, Annie starts sending sexy pictures to Jeff without explanation. Jeff is left to react however he reacts.

* * *

**Picking a Side**

"Seriously? You don't think that's just a little bit desperate?" Britta asked as Annie entered the study room. Most of the group members were already congregated, save for Shirley and Pierce who had a tendency to be late.

"No," Jeff said emphatically. "If anything it's the opposite of desperate. You have to be confident to do something like that."

"Do something like what?" Annie asked, sliding into her chair.

"Some girl sent Abed a naked picture of herself," Britta explained. "And _Jeff_ doesn't seem to think that's demeaning to women everywhere."

"Because it's not!" he exclaimed. "What a woman does with her body is her own business. You of all people should agree with me on that." Britta scowled.

"Yeah, sure, because degrading your gender to nothing more than meat for men to stuff and pack is exactly the goal early feminists had in mind."

"Stuff and pack?" he questioned.

"You know what I mean, and that," she gestured once again at Abed's phone, "is degrading. Back me up on this, Annie." All eyes turned to her, including a very curious looking Jeff. Annie ignored Britta, choosing to focus on him instead.

"You really don't think it seems desperate to send photos like that to a guy?" she asked, genuinely curious. Britta scoffed.

"So much for solidarity."

"Ignore Britta," Jeff said. "No, it's not desperate, because confidence is sexy, and like I said, it takes an extremely confident woman to send those kinds of pictures to someone." Annie contemplated this for a moment.

"But don't you think it kind of crosses a line?"

"There's only one line, Annie. People you sleep with, and people you don't. If anything, sending pictures like that is just picking a side. "

"Ugh," Britta scoffed.

"What are you going to do, Abed?" Troy asked, bringing the conversation back around.

"I don't know. By nature I like it when people make their intentions clear, since I'm not so good with subtle cues, but this woman has always reminded me of Natalie Portman's character in Garden State."

"So? Natalie Portman is hot," Troy argued.

"Yeah, but I hated that movie."

"You should give her a shot," Jeff jumped in. "Or at least take her for a test drive before you turn her down."

"Pig," Britta shot. Jeff smirked, clearly just trying to get a rise out of her at this point.

"I'll consider it. She was good in Black Swan, so that gets her some points."

"Abed, you realize this girl isn't actually Natalie Portman, right?" Annie asked.

"_No_," he said with forced sarcasm. "I'm Abed, I think _everyone_ is from the movies."

* * *

Annie laid on her bed, highlighting passages in her History textbook when her mind began to wander. The whole Abed/Naked Natalie Portman situation had happened earlier in the week, and since then Abed had gone on a date with her. It turned out she was more like Natalie Portman in V for Vendetta than Garden State, which freaked Abed out and he was forced to end things, but still, her success in getting Abed's attention like that was sort of fascinating to Annie.

Annie was somewhat of a novice when it came to attracting men, despite knowing she had all of the physical attributes necessary to be quite successful in that department. She had a great rack, this she knew beyond a shadow of a doubt, and although she'd taken more efforts recently to play up those particular characteristics, they still hadn't been yielding the results she was hoping for; namely, getting Jeff's attention. No matter how low her top, or how tight her cardigan, he never seemed to give her more than a cursory glance. It was becoming quite frustrating for the girl who prided herself on being good at everything.

Annie set down her textbook and pulled herself off the bed, wandering to her mirror and taking a good look at herself. She pulled her top off, leaving her in a lacy pink bra and skirt. She had great boobs. _Really_ great boobs. If porn stars had boobs like hers, the breast enhancement industry would go out of business.

She looked over at her phone laying on her bed and bit her lip. Jeff _had_ said he found it sexy when a woman was confident enough to send pictures like the one that chick sent to Abed. She wondered if he would feel the same way if she was the one doing the sending.

She heard Jeff's voice echo in her head: _"There's only one line, Annie. People you sleep with, and people you don't. If anything, sending pictures like that is just picking a side. " _

Maybe it was time for her to finally pick a side. Maybe that's what Jeff was waiting for.

Annie grabbed her phone and turned the camera to her. She held it high over her head, peering up at it with wide-eyes and a pout, and clicked to take the picture.

"Ugh," Annie groaned when she looked at it. From that angle she looked like a desperate bush-baby, with gigantic eyes and weird, butt-like cleavage.

She turned the camera on herself again, this time holding it out in front of her and giving it a sultry gaze.

"Eww, even worse," she mumbled to herself at this photo. All she could really see was her bad attempt at a sexy face and her gigantic forearm blocking half the picture. She really should have practised cam-whoring more often.

"One more time," she said softly. This time she just put on a natural-looking smile, quirked her brow, and held the camera slightly overhead. She smiled when she saw it—she looked playful, kind of cute, but still sexy, and her boobs looked freaking fantastic. She deleted the other two photos and pulled her shirt back over her head, laying back on her bed and contemplating her next course of action.

"To send or not to send," she muttered aloud. She opened up her text conversation with Jeff and composed a few test messages.

_Just thought you might be interested in this..._

Too casual.

_Hey cowboy, looking for some fun?_

Too prostitute.

_Jeff... _

Too timid.

_Decided to pick a side. _

Perfect.

She attached the photo, and before she had a chance to second guess herself, she pressed send.

And then her stomach dropped.

"Oh crap, oh crap, oh crap!" she moaned to herself, her stomach doing flips. She clicked around on her phone, seeking some sort of 'erase' or 'time machine' app, neither of which seemed readily available to her.

Then she just stared at the screen, hands shaking, eyes wide, barely breathing as she waited for something, anything to happen.

Hours, days, years seemed to pass with nothing, nothing, nothing.

And then it buzzed in her hand. Annie gasped when she saw she had a new text message from Jeff. She was so not prepared for his reaction.

_Jeff Winger: I can see that._

What? He can _see that_? What the hell does that mean?

Annie's breathing came in uneven spurts as she blinked and re-read the message over and over again, trying to figure out all of the potential meanings of his reply. Why was he making this so difficult?

The phone jolted in her hand again.

_Jeff Winger: You sure about this?_

Annie swallowed hard. _No, _she thought to herself.

_Annie Edison: I'm sure_.

Another moment.

_Jeff Winger: You want to come over?_

Holy crap.

Holy crap!

Annie's mind raced a mile a minute. _Holy crap!_ What the...what? What now? What did that mean? Did he want her to go over and..._have sex_ with him? Did he want her to come over so he could let her down in person? Did he want her to come over for a game of crazy eights? What did he mean?

_Annie Edison: Come over and do what? _

She nearly bit a hole in her lip waiting for his response.

_Jeff Winger:_ _Whatever we want._

Annie tried not to hyperventilate. She really, really did.

_Annie Edison: I'll be there in an hour_.

His reply came a few seconds later.

_Jeff Winger:_ _Looking forward to it._

Annie flung her phone down onto the bed and raced out to the bathroom. She needed to shave.

**End**

* * *

_Response to a Ficcy Friday (Ficcy Sunday?) prompt from rashaka. Hope you liked it! Let me know :)_


	2. Chapter 2

**Title: **Picking a Side (2/2)

**Rating: **NC-17

**Spoilers/Warnings: **None

**Disclaimer: **I don't own Community, yo.

**Summary: **Inspired by a suitor of Abed's, Annie decides to send Jeff a risqué photo in hopes of persuading him to give her a shot.

**A/N: **I'm kind of hopeless against peer pressure. Here's part two. Enjoy!

* * *

**Picking a Side Part 2**

He rested on his stomach, and she on hers, and they watched each other in the dimly lit room.

His hand ghosted over the curve of her back, stopping before her skin disappeared under the low-slung bed sheet. Morning sun began to creep into the room, casting soft shadows, making her pale skin seem even lighter, almost iridescent.

She shivered, his fingertips grazing her lightly enough that it was nearly a tickle along her spine, and she focused on steadying her breathing as he reached the bottom of her tailbone before working his way back up once again.

Her head rested on the back of her hand, and she watched him as he watched her. The pillow made an indent on her face that she wouldn't notice until later in the morning when they finally pulled themselves out of their cocoon in bed to start the day.

It had been a perfect night. Annie had fallen asleep naked, luxuriating in the soft cotton of the bed sheets against her sensitive skin. She discovered that she liked to sink into the sheets and experience them. The sheets, Jeff, everything about the scene was so far removed from her buttoned-up way of living. Prior to the night before, she wore pyjamas to bed every night without fail. She sunk into the mattress and pillows, but the sheets were only there to keep her warm.

Now, she realized, the sheets were a part of the whole experience. They teased and tempted her, and made her feel at once fully exposed and safely covered.

When she rolled onto her back, she thought about pulling the sheets up to cover her now exposed breasts, but found the cool air of the room to be quite pleasant. She felt open and sexy and available with her breasts uncovered, and she wanted to touch them and to have Jeff touch them too. The covers now rested on the very bottom of her hip bones, only just barely covering her most private parts.

She allowed one hand to rest on her stomach. The skin there was so soft that it made her want to stroke it, which she did while watching Jeff the whole time. His eyes flitted between hers and her body, the covers also slung very low on his hips.

She traced her finger up over her diaphragm, grazing in between her breasts and back down again, caressing the dip between the two sides of her rib cage. She trailed them lower, circling her belly button before making a return trip to where she began.

Jeff wet his lips, and pushed himself up so he was on his side, resting on one arm, with a free hand ready to explore her body that was open and available for him.

She dropped her hand to her side, letting him take over.

He placed his palm flat on her lower abdomen. The heat of his hand was warm and welcome against the slight chill of the room, and its size made her feel excessively tiny. His hand covered a large portion of her stomach when his fingers splayed out. Occasionally, she loved that Jeff was a giant.

He bent his head down and placed kisses to the top of her breast and shoulder while his hand started a slow journey upward, fingers grazing hardened nipples before dipping into the crevice between her breasts and returning to her lower abdomen in small, intricate patterns.

He lowered his head and took a nipple into his mouth, lazily drawing circles with his tongue, laving it with affection, while he moved his hand up to palm her other breast.

Annie closed her eyes and focused on the sensations he was creating within her. She slowed her breathing, letting him lull her to a dreamlike state, a mix of arousal and relaxation. Jeff's lips left her breast and the cool air hit the wetness left behind, sending a shiver through her as he moved to offer her other breast the same attention.

Jeff settled himself alongside of her as he kissed and caressed his way down her body, his pink lips finding the alabaster of her stomach and leaving a soft trail there. Annie let one hand rest on his head, gently massaging his scalp with her fingernails as he worked lower, pushing the covers down and out of the way, his hand always a brief step ahead of his mouth.

Annie watched him lazily as he pushed her thighs apart, his hands smoothing over the soft, perfect skin he found there as he settled in between them, his lips falling to the dip between her hip bones, then to her inner thigh, and then into her warmth as his tongue eased out to stroke from opening to clit and back again.

Annie's breathing sped up a little more.

As he lavished her with attention, he braced his body with one arm while his other reached up, palming her breast, thumbing her nipple and drawing out quicker breaths and moans as he brought every nerve ending to life within her. Annie continued to run her fingers through his hair, gently, revelling in the feeling of the short, clipped strands against her fingertips.

He didn't bring her up all the way. He brought her to steady, deep breaths until he worked his mouth back up her body, settling his hips in line with hers, and pushing in. His lips grazed hers, not kissing, just moving together silently as their bodies worked together, his hips meeting hers with a small circular motion that he'd discovered she enjoyed the night before.

This was the fourth time they were doing this. The night before had been frantic at first, and then more calm, but to start they both skipped common pleasantries. Jeff woke up in the morning feeling like he'd cheated her a little bit of those romanticisms. As he met her gaze this morning, he sought to make up for that.

Annie felt a now familiar bubble of heat and pressure building within her, and she wrapped her legs tight around Jeff's waist, pushing up against him in efforts to relieve it. Taking the hint, Jeff ground down further into her, brushing her clit with his pubic mound on each thrust, watching as her eyes fluttered and eventually closed tightly, her mouth open in a silent cry as she tightened and pulsed around him once again.

It was a feeling he knew he wouldn't grow tired of. Not after waiting so long for her to be here like this with him.

He dropped his head onto her shoulder, picking up his pace as he finished himself off. Annie sighed contentedly in ear as he filled her, as though his release was as pleasing to her as is it was to him.

He thought about falling to the side, but she kept him wrapped up in her arms for a few moments, not letting him go. He settled on top of her, revelling in her skin against his, a welcome heat between them as their breathing fell into sync. She kissed his shoulder, then neck, and then tugged his earlobe teasingly between her teeth making him chuckle.

He rolled them, pulling her on top of him. She rested her chin on top of her hands on his chest, peering at him with a small, satisfied smile. His hands found her lower back, thumbs moving back and forth over the smooth skin there, fingers splaying onto her backside.

"Morning," he said, his voice low and gritty. She giggled and placed a kiss to his chest.

"Morning." He grinned and tucked a lock of her hair behind her ear, leaving his hand there to tug through the strands.

"I got the weirdest text last night," he joked. The pair laughed, and Annie flushed lightly, dropping her face into her hands. "Nuh uh, you don't get to be shy now," he teased. She peeked up at him with a small, timid grin.

"I've never done anything like this before," she said quietly. He swiped her cheekbone with his thumb.

"I figured." She watched him contemplatively for a moment.

"Would this have happened otherwise?" He bit the inside of his cheek, thinking about that for a moment.

"I think so," he eventually said. "I hope so." She let out a small breath.

"When?" He shrugged.

"Not soon enough."

* * *

Annie laid on her bed. It had been about a week since she had sent Jeff that photo. A week since she'd gone to his apartment with the expressed purpose of having sex with him. A week since they'd spent all night and most of the next day in bed together.

And things were still pretty good. The group wasn't even too bad when they announced their new relationship. There had been some expected push-back, but it wasn't as bad as it could have been. Annie figured enough time had passed after the whole Britta/Jeff thing that most of those concerns were null and void. Besides, Britta was with Troy now—Shirley didn't have a leg to stand on.

Of course, all of that good stuff didn't make it any easier when she told Jeff earlier that day that she'd be spending the night at home with Troy and Abed rather than in his bed.

She just didn't want to go too fast, for all kinds of reasons. She didn't want to smother Jeff, she didn't want to put too much pressure on their new relationship, and she didn't want her friends to think she was abandoning them. Even Troy and Britta took a night off now and again.

But now that she was laying in her own bed, she felt kind of miserable. It had only been a week, but she had gotten used to Jeff's Egyptian cotton sheets and his warm body next to (and inside) hers. She almost gave up and went over, but that flew in the face of all of her perfectly valid reasons for taking a night off.

She was pulled from her musings by her phone vibrating next to her. She opened the new text from Jeff and burst into laughter.

It was a picture of his brief-clad torso, with a post-it note on his stomach that read: So very, very lonely.

She quickly composed a response.

_Annie Edison: Poor baby._

A moment.

_Jeff Winger: Miss you. _

She smiled widely. Schmoopy Jeff was a sight to behold.

_Annie Edison: You saw me three hours ago!_

_Jeff Winger: You were fully clothed—doesn't count._

She rolled her eyes.

_Annie Edison: Is that all I'm good for? :P_

_Jeff Winger: Whose opinion do you want? Mine, or Little Jeff's?_

She laughed lightly.

_Annie Edison: Start with yours and work your way down._

_Jeff Winger: My opinion: I'm lonely and you're my favourite kind of company. His opinion: you're way too sexy to ever wear clothes. Ever._

Annie nibbled her lip. After a moment's thought she pulled her shirt and bra off, clicked a picture, and sent it off.

_Jeff Winger: Not fair. SO not fair._

She grinned.

_Annie Edison: So sleepy! See you tomorrow ;)_

_Jeff Winger: Pure evil._

She giggled and put her phone on her bedside table and went about getting ready for bed.

About half an hour later, her phone buzzed again. She squinted in the dark, opening up her most recent text from Jeff.

It was a picture of his brief-clad crotch with a post-it that read: Thank you for your service.

**End**

* * *

_Apparently I have no will power and when I allude to sex, I'm incapable of not actually writing it. I'm a perv, what can I say? Hope you liked it. Let me know!_


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